


Canon City Tales: Gwyndolin

by GoHt



Series: Canon City Tales [1]
Category: Dark Souls (Video Games)
Genre: Alternate Universe, Anal Sex, Come Inflation, Consensual Sex, Deepthroating, M/M, NSFW, Prostitution, Rough Oral Sex, Rough Sex, absolutely enormous ass, bulging, femboy, hyper
Language: English
Status: Completed
Published: 2017-08-19
Updated: 2017-08-19
Packaged: 2018-12-17 03:09:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,801
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11842716
Author URL: https://archiveofourown.org/users/GoHt/pseuds/GoHt
Summary: In Canon City, fictional characters from all walks of life live together. But the city is not for them. It's a city made for the perverted fantasies of the outside world. Everyone is inexplicably huge, and their appetite for sex is endless.Gwyndolin is a bit of a niche item, but the sort of customer who wants a piece of him will pay handsomely to get it. Seems like an easy job, but sometimes even a seasoned whore like Gwyndolin is surprised.





	Canon City Tales: Gwyndolin

**Author's Note:**

> This is one of the few pieces I'm comfortable showing online. I'm rather proud of this one, even if it's a bit sloppy, especially near the end. I should preface this story by saying that there is nothing of real substance here. It's all just indulgent smut. No real adherence to canon either, as I don't recall Gwyndolin having hips wider than his shoulders. Either way, I had fun writing this, and hope you have fun reading this.
> 
> Canon City Tales could become a series. It's really an avenue for crazy, crossover smut between whatever I like. 
> 
> Feedback on this would be greatly appreciated. I certainly want to improve and am trying to work on my flaws. Biggest flaw, of course, being actually working on these stories.

"I would appreciate it if you stopped staring and paid up."

Seemingly shaken out of his trance, the stranger retrieved his wallet from his back pocket and started fishing through it, gathering bill after bill. It was a fairly normal transaction, at least for this city. A back alley, someone willing to pay. Only thing different was the 'merchandise'. Canon City was known for its women of incredible size. It was a haven for a niche market and many would pay top dollar to even have the privilege to visit the place, let alone live there. Back alley deals like this were commonplace, with someone willing to pay good money to get their rocks off real quick after a night on the town. No need for a motel; when they were done, they were done. Transaction completed. 

What made this one so special then? It was simple enough. This was no well-endowed girl. 'She' was something completely different. They were dressed like any other alley tramp. Scantily clad, wearing toeless platform heels that showed off their painted nails and made them wobble awkwardly with each little movement, the prostitute eyed the stranger's wallet impatiently. One hand rested against their hip, which only drew more attention to their ridiculous figure. A pair of hips, on full display due to them wearing little more than a thong and a skirt that didn't even reach halfway across their immense backside. Wider than their shoulders, those hips were only the beginning, leading into a juicy pair of legs, and then thick thighs that enticed with every little movement. Of course, one could hardly mention this tramp without mentioning their gigantic ass. The thong did little to hide it, putting it on full display at all times. Pale, twin globes that wobbled around from even the slightest movement, so round and firm that it was difficult to believe such a beauty could be real.

There were no breasts to speak of. In fact, the curves ended right at the hips, moving inward at a sheer slope, leading into their skinny figure, flat chest, and feminine features. Despite having no breasts to speak of they still wore a top, with only thin strips of fabric to cover their nipples. Last but not least were a plush pair of lips, covered in dark blue lipstick and currently pointed downward in a frown. The stranger had paused again, seemingly contemplating their choices. "Are you going to pay, or not?" Their other hand reached forward, palm open, ready to accept their payment and get to work. This was an expensive transaction. This prostitute, this Gwyndolin, was a bit more niche than even the girls of Canon City. Mostly due to the fact that Gwyndolin wasn't a girl at all. 

Oh, he acted like one alright. Dressing in feminine clothes, wearing heels, applying lipstick. It was all for the act, and it took heavy advantage of his gifted figure. While it was hard to determine his expression due to the crown he wore at all times, which obscured his eyes, he seemed pleased as the stranger finally handled the money over. After counting it up, Gwyndolin approached, heels clacking against the concrete as he stood close to the stranger. Chuckling, he waved the cash in front of his face, "See? Was that so ha- Mmmmf!" An arm wrapped around his thin waist, bringing him even closer. A kiss was forced on his soft lips, a stranger's tongue invading soon after. He made no attempt at pushing away. Now that money was exchanged, he was someone else's property. That was readily shown as the stranger's free hand smacked firmly against his huge backside, causing a massive ripple upon impact. That hand squeezed and kneaded one of those soft globes, grabbing firm handfuls, fingers sinking so deep into that plentiful ass that it almost appeared to disappear, flesh bulging from between the customer's fingers. 

A firm smack echoed throughout the alleyway, as that same hand lifted, and then brought itself down hard over that cheek. It bounced and rippled from the impact, leaving quite the mark thanks to Gwyndolin's pale skin. Breaking the kiss, the boy gasped, slightly resisting against the vice grip on his chin. "N-no kissing~" He barely stopped the customer from leaning in for another, hungrily sliding his tongue into the young thing's mouth, all while his hand happily played with the streetwalker's massive ass. Dark blue lipstick stuck to the stranger's lips, as he kept up the feverish kissing, completely dominating poor Gwyndolin's tongue. But it wasn't going to last very long, as the stranger was evidently impatient, pulling a moaning Gwyndolin from the kiss and placing a hand against his flat chest. Pinching one of the boy's nipples, he caused the scantily-clad 'princess' to shake and squirm, as he reluctantly lifted a hand away from that fat ass to guide him downwards.

Eventually, Gwyndolin got the idea, sitting on his knees in front of the paying customer, still squirming from his vice grip on that one nipple. Even through his tube top it was painful. Leaning his head back, Gwyndolin's lips hung open, tongue hanging at the side, waiting for whatever the stranger had to offer. A thumb pressed against his thick bottom lip. For a boy, Gwyndolin had many feminine features. Most noticeable of course being his massive pair of hips, but it was hard to ignore those soft-looking lips, thick and covered in dark lipstick. Gwyndolin's lips opened as the stranger pressed down, a finger sliding into his mouth, which he eagerly played with. His tongue licked, and his lips wrapped firmly around it, sucking desperately on the offered finger, as if to demonstrate his experience. 

This demonstration seemed to please his customer, as soon that finger slipped right out, coated in lipstick and saliva. Gwyndolin placed a hand over the man's belt, starting to pull and tug, desperate to see what the deal with that bulge was... No way he was that big, it had to be some kind of act. "Perhaps you would like to show it to me?" Cooed the boy, tongue sliding around his lips in a gentle circle. "Come now... You paid... There is no need to hide it~" The stranger pushed Gwyndolin's hands away, loosening the belt himself, that bulge becoming firmer and more distinct. Still, even with the bulge Gwyndolin could hardly believe the stranger could be that big. It had to be some kind of joke. 

"Do not feel shy... If I turned down every below-average cock I would be out of business, let me help yo-uuu... Hoo..." Flopping out from those pants was a truly massive member, more likely to belong to a horse than a man. Hanging down between the stranger's legs was a thick, semi-erect cock, which twitched and throbbed already. The tip alone was nearly touching the ground, its incredible thickness giving it the appearance of an extra leg. A thick, heavy pair of balls, mostly responsible for the bulge, nearly reached to the man's knees. So round and firm that Gwyndolin was already drooling at the thought of getting his lips around them. His heart skipped a beat as the stranger moved closer, pressing Gwyndolin's cheek against the side, warmth emanating from him. The scent was laden with sex, clearly showing some experience. Gwyndolin doubted he was the stranger's first victim for the night, with how fresh the smell was. It smelled like women...

"I...I see..." Muttered Gwyndolin, placing both hands around that thick shaft, holding it firmly and starting to tug downwards. It was so thick he could hardly fit one hand around it, having to use two to be somewhat effective. "You are impressive... Apologies for doubting you, kind stranger~" This was so surreal. It had to be massive... Three feet long, at the most. Hard to gauge exact length when you were drooling over a fat cock. Gwyndolin's thong stretched out even more, a small, but noticeable bulge growing against the fabric. Usually Gwyndolin treated this as work, but this was more like a treat than a job. Not that he actually had any intention of taking the whole thing, but the simple novelty of such a monster cock got him excited for once. He would certainly rather have a customer that was too big, rather than one that was too small. At least the oversized cock was fun to play with. 

Soft, lipstick covered lips continuously kissed along the length, moving from base to tip, leaving firm marks in the process, dark and very clearly defined. His tongue flicked across it between kisses, all while his hands continued to jerk up and down, smearing saliva and lipstick all over that burgeoning cock. Hard to believe it was only semi-erect. Already it felt so thick and warm, throbbing with desire. Gwyndolin could hardly keep down the urge to shove the whole thing down his throat. Such a thing would be impossible, of course. But still, the idea was there. For now he would satisfy himself with kissing it, smearing more and more of his lipstick all over it, leaving dark marks all over it. Soft, pale hands continued to move up and down, tugging on it. He could hardly jerk the whole thing in one smooth motion. The stranger was just so long and thick, he still had a hard time believing it.

A hand on the back of his head brought Gwyndolin out of his trance, fingers raking through his silver hair, up and down, before nudging against his golden crown. Frowning, he playfully swatted that hand away. "The crown stays~" That hand reached down, fingers curling, bunching up locks of hair and pulling Gwyndolin back. With their free hand, the stranger lifted their massive cock, all three feet laid out before the streetwalking 'princess'. "Ahhh! Be gentle, you are pulling on my hai-!" Face brought forward, Gwyndolin felt his lips pressing against the wide tip, which started to roll and grind against them, practically begging for entrance. He had a choice of clenching his teeth and refusing it, or opening his mouth and accepting the whole thing. Gwyndolin's jaw hurt just looking at that monster, its thickness alone enough to make him wonder if he could take it at all. But the temptation was still there, and soon enough his lips started to part. The stranger showed some restraint at this, not shoving his entire cock down his poor little throat. It was merciful, considering they could have certainly shoved the whole thing in, if they so desired... 

Carefully taking it in, little by little, Gwyndolin felt a slight pain in his jaw. Hardly as bad as he thought it would be, but definitely there. Plump, girlish lips were stretched wide open, a tight vice formed around that massive cock, smearing lipstick lightly over their skin. Gwyndolin leaned forward, stopping just shy of his throat, which in comparison meant a very small portion of the stranger's cock was actually inside the boy's mouth. Then again, generally the strangers he deepthroated didn't sport a yardstick for a cock. With only the first few inches or so, he got to work, bobbing his head back and forth eagerly. Wet, slurping noises sounded out, his work no doubt sloppy thanks to being unaccustomed to such a girthy cock. Spittle flew out from between his lips, leaking down as he moved his own head back and forth. Still nearly three feet away from the stranger, Gwyndolin realized he had a lot of work ahead of him. 

Even trying to throat this massive prick was a chore, getting the tip in enough to make the experienced streetwalker choke and gag. Hard to believe all those skills, that honed whoring ability, seemed to just fall apart when faced with a monster cock like this! Gwyndolin finally had to pull back all the way, coughing and sputtering, that cock hanging down between the stranger's legs, only a small portion covered in saliva and with a very distinct ring around Gwyndolin's furthest point. "My apologies... Ahhh..." He continued to cough, unable to even finish his sentence. "Y-you are just so impressive, I can hardly work... Give me just a moment~" Somewhat dreading going back, Gwyndolin sat there in front of him, taking deep breaths, and trying to work up the courage to go back in. The stranger seemed patient, Gwyndolin noted, standing there with a hand gently pressed against the back of the boy's head, just waiting for him to muster up the desire to suck this massive cock. 

Once those plump lips of his opened up, the stranger surprised Gwyndolin, thrusting forward with a great amount of force and stuffing about half of their titanic cock down his poor little throat. Gagging loudly, Gwyndolin’s face started to turn red. Though the stranger could not see his eyes past that golden crown, a light stream of makeup running down his cheeks gave him a good idea of what he looked like. Eyes watering, the fat-bottomed prince tried to pull back, only for the stranger to push them deeper. A very thick, very noticeable bulge ran along the boy’s neck, sliding ever deeper. This was the most he’s ever swallowed, and the stranger was hardly past the halfway point. Seemed the stranger wanted to prove him wrong, showing that he COULD in fact take the entire thing. At this point, Gwyndolin wondered if this actually counted as “taking it’. 

Lifting his hands, he placed them against the stranger’s thighs, hacking and gagging around his huge cock. Gwyndolin was briefly afraid of choking on this massive dick, but his paying customer was thankfully kind enough to pull back, rolling his hips back just a bit, allowing Gwyndolin to take a very, very deep breath. Then, all bets were off. The moment the streetwalking femboy had sufficient air, the stranger tried to stuff the entire thing back in. By now, passing out seemed to be the most likely option, as the stranger had finally managed to slide the entire three foot monster into his throat. Gwyndolin gagged as he pushed right against his lips, huge, cum-swollen orbs resting against his chin. Spittle sloppily poured between Gwyndolin’s lips, as he was more concerned with breathing than actually sucking this stranger off. 

Shame that they needed to breathe, too. Just the idea of taking the entire thing was unbelievable to Gwyndolin, and yet here he was, doing it! Though, he could hardly enjoy it when the stranger refused to bring him back up for air. Just when it seemed like he would pass out, they finally let him go, the prince pulling all the way back, stopped just shy of the tip. Once again there was about three feet of space between them. Hard to believe he could take that much. It definitely felt strange, to have it sliding into his stomach, bulging against his belly and making a very clear indentation. No amount of preparation could have helped Gwyndolin with this monster. Still, it was gratifying to see a dark blue ring around the base of his cock, a marker to show that Gwyndolin had done it, indeed. Hopefully his customer’s needs were fulfilled, and he could go back to something that was doable. 

Clearly, that was not the case. Moments later Gwyndolin was forced back down. The difference being, he wasn’t trapped at the base for very long, as the stranger gleefully retracted his monster cock from his throat all in one motion. Inch after inch dragging its way out of his throat, until Gwyndolin could breathe again. After a brief moment of rest, the stranger shoved the poor boy back down again, pulling out with even more force than the last. Rapidly increasing in pace, the stranger was soon shaking Gwyndolin’s head back and forth, happily using his throat like he would use any other hole. Which sparked just a bit of ire in the young prince, though, he could hardly complain at the moment. He could breathe, which was a step up from what the stranger was doing before. Slurping, gagging noises filled the alleyway, as that was simply all the prince could do, with his throat utterly filled and his lips spread wide by a girthy cock. All the prince could hope to do was endure the abuse and come out of this still conscious. A smear of dark blue ran across the entire shaft, showing the prince’s good work quite clearly. Despite the borderline abusive treatment from his customer, Gwyndolin was quite proud of how well he was taking this! Merely admiring his own work. Now, he could proudly say, “I deepthroated a three foot cock” to his fellow whores and be showered with praise. Of course, he needed to take pictures, first.

A telltale throbbing sensation in Gwyndolin’s throat alerted him to the impending flood. In all this commotion he had yet to consider what would happen when the stranger finally climaxed. As his pace increased, the prince was further reminded of his customer’s virility by the massive pair of balls slapping right against his chin. So big that he couldn’t even fit his hands around one of them, and no doubt churning up a load to remember at this very moment. Maybe out of desperation not to drown in cum, or maybe because he wanted a chance to actually taste his cum, Gwyndolin tried to pull back. But the stranger was having none of it. A vice grip on the back of the prince’s head forced him to the base again, an all too-familiar sensation of choking on dick overwhelming him. Light, one or two inch thrusts were all that he had now, at such a rapid pace that the stranger’s balls were rhythmically smacking against the underside of the whore prince’s chin. 

When it finally happened, Gwyndolin was not ready in the slightest. It happened so quick too. One moment the stranger was face-fucking away without a care, and the next moment, Gwyndolin was pressed so firmly against the stranger’s pelvis he might as well have been glued there. The first blast was just that: a blast. Like a firehose going off, a sensation of warmth filled the young prince’s stomach. That cock throbbed and bucked, balls struggling to release every last drop of cum straight down Gwyndolin’s throat. Soon enough it got to be too much for even the experienced slut, and eventually, it was spraying out the side of his lips, every rope of cum bringing with it a waterfall of thick, white jizz that formed a puddle between the two. Meanwhile Gwyndolin’s already distended stomach started to balloon, growing rounder, and fuller with each consecutive blast. It never seemed to end, either, with Gwyndolin struggling to remain conscious as the stranger kept his head held down, forcing him to swallow as much as he could, though about forty-percent of his load had ended up on the ground simply because Gwnydolin was overwhelmed. With Gwyndolin’s belly nearly bumping against the ground, the prince hardly moved, still on his knees and almost limp. Figuring this was ‘good enough’, the stranger finally released him, allowing the prince to gasp for air. 

Leaning forward, Gwyndolin pressed his hand against his belly, which sloshed and wobbled with every slight motion. Coughing and sputtering, it was no surprise to see jizz was pouring out of his mouth. He had never swallowed so much in his life, and wasn’t even sure he could keep it all down! Groaning at the warm, ‘full’ sensation that enveloped him, Gwyndolin would, at times, cough up some more cum, joining it with the mess below, which he was currently stooped in. His stockings were messed up, as were his heels, but that was common enough. If Gwyndolin wasn’t prepared to get his clothes dirty, he would have never taken this job. Though for a brief moment, he was perhaps regretting his career choices. Seeing that monster of a cock dangling in front of his face, Gwyndolin let out a soft grunt. “C-Could have warned me, you... idiot...” He coughed up again. At this rate he’d just expel all of it, as his belly was already starting to shrink. “You cum too much...” he muttered, coughing up more and more, before finally continuing, “and you nearly made me choke. I feel I should ask you to pay extra, for how much you put my life in danger! You...” Closing his eyes, Gwyndolin sputtered again, a few more strands of that thick liquid forced back up. His belly had shrunk back down to its normal size by now, most of its contents spreading across the pavement in front of him. 

Wiping his lips, Gwyndolin looked up at his customer, who was still throbbing. That insanely massive cock seemed insatiable. If he was to encounter more customers like this, Gwyndolin would have to increase his rates. No doubt the ‘princess’ would be totally exhausted by this end of this. Heck, he might not even be conscious when his customer finished. Sighing heavily, the curvy prince carefully rose to his feet, making sure he had even footing on his heels before starting to walk over to the nearby dumpster. Heels clacked with every step, and he deliberately wiggled his hips side to side, drawing the customer’s eye towards that massive rump. Bending over that dumpster, the prince grunted, starting to shake his backside, back and forth, back and forth. Those twin globes wobbled with even the slightest movement. “Come now... this is what you came for, is it not?” Gwyndolin taunted, reaching a hand back, sliding long, slender fingers between his cheeks and spreading one apart. His hands sunk so deep into that pale moon that they practically disappeared. The thong he wore barely kept things covered, as the customer could clearly see the outline of his pucker. Despite obviously being a whore, it seemed pristine and untouched. Just one of the many wonders of this city of canons. 

A gasp escaped the pale boy’s mouth as the customer pushed forward, placing himself as close to Gwyndolin as he was able. That huge pole drove between his cheeks, almost completely enveloped by them, only to peek out the other side, running along the length of his back and almost touching the back of his head. All it took for that immense girth to be completely surrounded was for the customer to reach over and squeeze both of those cheeks, pressing them tight together, like a vice, around his cock. An intense throb ran along its length, Gwyndolin’s lips hanging open for a moment as the customer lightly rolled his hips back and forth. Thanks to Gwyndolin’s efforts, he was nice and slick, coated in a thick layer of saliva that allowed him to easily glide between Gwyndolin’s huge pair of moons. “Going to keep teasing me, are you? Not ready to take your prize just yet~?” Egging him on was probably the last thing Gwyndolin needed to do, but here he was, doing it.

The incredibly thick prince shivered as warm strands of pre-cum dribbled onto his back, the silent customer continuing his slow, gentle hotdogging. There was no reason for Gwyndolin to be complaining, as this gave him some time to rest. This moment to catch his breath did the opposite of what it was supposed to do, as now, Gwyndolin was waiting for the inevitable, for this oddly silent, oddly generic stranger could get to the main event any moment. All it would take is a few quick movements and Gwyndolin would be taking the biggest cock he’d ever taken. It was heart-pounding, waiting for this stranger to get bored with just the rubbing... Gwyndolin expected it to happen fast.

What he never expected was that it would happen slowly. A little gasp escaped the prince’s lips as the stranger’s fingers slipped between his thong. The straps were stretched tight around his hips, and if he were just a few inches wider it would probably have snapped in two from how tight it was. As that thong was rolled down his thighs, Gwyndolin let out a little whimper, betraying just a hint of fear at the idea of being speared by this huge cock. Gwyndolin had struggled immensely with just a blowjob. How could he be expected to take the whole thing? Gwyndolin’s biggest customer wasn’t even close to this guy’s size! It would not take very long for the silver-haired prince to feel his customer pull back. He had to stand a fair bit away, length and all... but eventually he felt the fat tip of that cock press against his asshole. Gwyndolin's back arched a bit, and he briefly contemplated moving away, but now was not the time to get cold feet. 

Now was the time to prepare himself, and hope for the best. Gwyndolin’s fingers wrapped tightly around the edges of this dumpster he had so unceremoniously laid himself across. Feeling that cool metal against his skin, Gwyndolin was starting to wish he had chose something more comfortable to lie himself across. His legs quivered a bit as the stranger started to prod, little test thrusts placed against his tight asshole, which refused entry each time. Strong muscles tried their hardest to prevent entry. At this point, Gwyndolin would have preferred if the customer just impaled him all at once, instead of doing it gradually like this. At least then they would get it out of the way and be able to get this over with. As it stood, the stranger was driving the moon-worshipping cocksucker insane by just gradually slipping inside of him.

No matter how much his body resisted entry, it would eventually be weakened. Repeated thrusting and prodding against that tight hole meant that the customer’s oversized cock eventually managed to slide in, gradually widening Gwyndolin’s hole, little by little sliding inch after inch inside of him. Gwyndolin’s teeth started to grit, grunts and moans escaping through the gaps. Barely even close to the quarter point and already Gwyndolin was struggling. It was painful, obviously. But more importantly, the burning sensation deep inside of him, the pleasure that followed, made it hard for Gwyndolin to tell him to stop, or to slow down... His quivering legs, pleased moans, and that tiny cock between his legs fully erect, all signs that Gwyndolin enjoyed this more than he wanted to.

The stranger’s arms wrapped around Gwyndolin, the streetwalker pulled away from the dumpster just as the stranger had reached the halfway point. Already his flat stomach was just slightly distended with the outline of his silent partner’s cockhead. Both of the boy’s wrists were gripped firmly, and his arms were pulled back. Gwyndolin had been in this position before, but never taking a customer this huge. It was an enlightening experience to have his arms pulled back all the way, his body supported only by the customer’s grip and whatever leg strength the prince could still muster. Then it happened... a clap. The sound of the stranger’s pelvis hitting Gwyndolin’s fat ass, the sound of those oversized balls slapping against his thick thighs. The only sound that Gwyndolin managed to make was a little groan, those plump, lipstick-smeared lips hanging wide open. He hardly wanted to look down, as he knew his stomach was bulging obscenely with such an impossibly huge dick fully sheathed inside of him. 

But eventually he had to, his head rolling forward as the stranger started to thrust. One after another, at a grueling pace. Not fast, but rather slow... Pulling out gradually each time to a little under the halfway point, and then slamming everything back in. With each thrust, a grunt followed from Gwyndolin. He continued to grit his teeth. Drool stuck to the sides of his mouth, he continued to tear up, allowing makeup to stream down his face, and continued to try and hide his moans. He was failing pretty spectacularly in that regard, as Gwyndolin just couldn’t keep it down. His boyish voice rising into higher pitches, every thrust drawing out a sweet song from that lovely voice of his. Gwyndolin’s stance widened a bit as his legs lost their footing, but thankfully the stranger was there to tighten his grip and keep Gwyndolin supported. Even if the only thing supporting him now was the sheer length of his customer’s cock, and the strong grip he kept on his wrists. 

It was surprisingly quick for Gwyndolin. Usually it took a very long time, with lots of work, to draw out a hands-free orgasm from him. Maybe the prince was just a size queen, and he never knew it. Whatever the case, he felt the telltale signs well before it happened. The pressure building inside of him, how each thrust from the stranger built it up even more, how his tiny cock was throbbing and bucking wildly... when it finally released, Gwyndolin’s mouth opened all the way and he just let loose. No attempts to hide his moans, just crying out. His ass clenched around the stranger tight, while his cock pumped out a few weak strands of cum. A little drop compared to the gallons his oversized partner could put out. 

But things were not even close to done for the crossdressing prince. The stranger seemed to last much longer than him. Even if his ass felt sore, and oversensitive from that orgasm, he received no rest. Due to the risk of collapsing, the stranger lowered to the floor, letting Gwyndolin sit on his knees instead. The prince’s arms went limp as the stranger let go of them, moving his hands to the boy’s hips and gripping him hard. Instead of the slow, agonizing thrusts from before, Gwyndolin was treated to a proper fucking. The stranger’s thrusts both quick and deep, making use of that incredible length. Gwyndolin felt stretched-out and used, leaning forward with only the stranger’s hold the only thing keeping him from collapsing on the ground. His stomach moved back and forth, that huge cock distending it over and over again. Gwyndolin would be worried about his health if he were anywhere else in the world, but this city just seemed to make impossible things... possible. 

His massive ass rippled and wobbled from each thrust, providing an adequate cushion for the stranger to thrust into. Soft, round, and incredibly huge... Gwyndolin was perfect for this. An ass that would make regular women jealous and put him on par with the curviest of girls in the city. It provided this nice “smack” every time the stranger’s hips collided with it. The customer’s hands would sometimes roam from those wide hips, tracing down Gwyndolin's curves and taking happy handfuls of the boy’s ass. Digging his greedy fingers into all of that pale flesh, letting it disappear into its doughy exterior. Gwyndolin was trying his best to stay conscious, and even tried to tease the customer a bit. Of course that attempt fell flat when Gwyndolin realized his attempts to speak were in vain. Any words he tried to form just came out as incoherent moans and grunts. 

A massive surge went through Gwyndolin’s body, and briefly, he had wondered if something inside him broke.. It would not be all that surprising. But no, what Gwyndolin would soon realize, is that he was feeling the stranger’s cock, throbbing inside of him. It continued to do this, growing more intense just as the stranger’s thrusts started to speed up. Gwyndolin could hardly believe it, but the stranger was preparing to cum again. If it was anything like his first climax, then Gwyndolin knew he would be stuffed full. The stranger pressed firmly against the curvy boy, thrusts growing deeper, and quicker, as his customer started to lose control of themselves. Gwyndolin shut his eyes and just prepared for the coming flood.

What a flood it was, too. A few more bucks from that cock and suddenly his insides were plastered white. An intense stream of cum blasting against the walls of his stomach, followed by another, and another. His cock was like a firehose, and Gwyndolin was just too tight around his cock for anything to escape. So, he was just forced to take it all. Pump after pump rounded Gwyndolin’s belly out, groans and moans escaping the streetwalker’s mouth as he felt the sensation of being stuffed full of cum once again. This time the sensation was intense enough to draw another orgasm from the boy! It just seemed never ending, with the stranger pressed tight ot his backside, with every intent on pouring every last drop into Gwyndolin. Little by little Gwyndolin’s stomach grew, until finally it was touching the ground, and the huge bulge that his customer made in his belly was just a mere bump near the top of it. The pale boy felt utterly stuffed, enough where the weight of his stomach was enough to finally bring him down a bit. Though he couldn’t lie down all the way, simply due to how his stomach propped him up.

When all was said and done, Gwyndolin was panting heavily. His arms placed on either side of his oversized stomach, he let out a groan. The stranger seemed pretty satisfied, at least, and gave the boy a final smack on his ass before starting to pull out. Gwyndolin tried his best to voice his concerns with that, but it was much too late, and when he finally managed to pull out the side effects of such an intense session became quite apparent. Stretched so much, it was no surprise that Gwyndolin’s ass gaped wide. And with nothing left to contain the pressure, a thick waterfall of cum started to ooze from his thoroughly-fucked hole. Gwyndolin’s quivering legs spread out, and he finally started to lower, his stomach starting to gradually shrink as the stranger started to stuff his massive snake back into their pants. The fat-bottomed prince took a deep breath and managed to speak, finally... “Thank you... come again...~” He said, having this big, goofy smile on his lips. 

The stranger was certainly not the type to cuddle. In fact, he was gone before Gwyndolin even knew it. But it seemed he was at least a little nice... considering there was an extra wad of cash placed beside Gwyndolin’s face. Only trouble now would be getting home like this... suppose he could just wait here, let it drain a bit...

Hopefully there were more guys like that around here. Gwyndolin was feeling pretty confident in his ability to take huge cocks now, despite being completely terrified of it before. Only thing he needed to do was raise his rates... If he was gonna be this exhausted after every session, he needed to be properly compensated!


End file.
